Ethyl Acetate → methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate

HRID 2404282노트

반응식

HRID 2404282 반응식
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[NH:24][CH3:25].C(OCC)(=O)C>O1CCCC1>[CH3:25][N:24]1[C:15]2[CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[CH:22]=[CH:23][C:14]=2[NH:13][C:1]1=[O:2]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone2회HCID 57835341Methyl 4-amino-3-(methylamino)benzoate

생성물 1

HCID 67151300methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate수율 64.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add carbonyl diimidazole (567 mg, 3.50 mmol) to a solution of methyl 4-amino-3-(methylamino)benzoate (586 mg. 3.19 mmol) in tetrahydrofuran (20 mL) at room temperature. Stir the yellow solution at room temperature for 16 hours. Add carbonyl diimidazole (500 mg, 0.96). Stir at room temperature for 4 hours. Add ethyl acetate (75 mL). Wash with 10% citric acid (5 mL), 1N sodium hydroxide (5 mL), and brine (5 mL). Dry the organics over magnesium sulfate, filter, concentrate, and dry under high vacuum to yield a crude yellow solid (690 mg, 100%). Triturate this crude solid with ethyl acetate (10 mL). Filter the precipitate and dry under high vacuum to yield methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (422 mg, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 3.46 (s, 3H), 3.92 (s, 3H), 7.12 (d, J=8.21 Hz, 1H), 7.68 (s, 1H), 7.84 (dd, J=8.31, 1.47 Hz, 1H), 9.87-10.03 (m, 1H).

후처리

  1. stirringStir at room temperature for 4 hours
  2. washWash with 10% citric acid (5 mL), 1N sodium hydroxide (5 mL), and brine (5 mL)
  3. dry with materialDry the organics over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customdry under high vacuum
  7. customto yield a crude yellow solid (690 mg, 100%)
  8. customTriturate this crude solid with ethyl acetate (10 mL)
  9. filtrationFilter the precipitate
  10. customdry under high vacuum

출처 및 근거

ORD 기록
ord-4fa189988f3e4a2c960022e9cd06199b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802690B2

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